What’s the real value of a college degree in 2026? Is it just about the paycheck, or is there something deeper we’re missing in the ROI calculation?
In this Q&A episode, Joe and I tackle one of the most consequential financial decisions […]
Category: Real Estate
#674: Remember When Inflation Was High and Rates Were Rising? [GREATEST HITS]
Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.
Today’s letter R stands for Real Estate. This episode originally aired in May 2022, but the insights on long-distance investing remain just as relevant for anyone feeling priced out of their local market.
We tackle the five biggest […]
#667: Should You Ever Get a 50 Year Mortgage? – with Dr. Karsten Jeske
Home prices have outpaced wages for more than a decade, and first-time buyers are stretching further every year. Now a new idea is entering the conversation, the 50-year mortgage. It promises lower monthly payments, yet it reshapes everything from equity growth to long-term risk.
In this episode we sit down with Karsten Jeske, PhD, CFA […]
#661: Q&A: Rebuilding After Debt Overload and a Near-Miss Foreclosure
When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navigating all of it at once, from a near-foreclosure to a luxury car payment that’s strangling her budget. Her question is simple but enormous, how […]
What’s Up With This 50-Year Mortgage?
I’m just going to come straight out of the gate with a hot take:
If you need a 50-year mortgage, you can’t afford the property.
Before you grab your pitchforks, let’s explore the new concept of a 50-year mortgage, which just entered the zeitgeist this week.
We’ll run the […]
#653: Radical Transparency in Real Estate Predictions [GREATEST HITS]
What happens when we actually check our predictions? In this episode we play clips from our 2023 conversation with Scott Trench from BiggerPockets and ask the uncomfortable question: were we right?
Two years ago we made some big calls about the housing market. Mortgage rates had doubled. Prices hadn’t crashed. Inventory was vanishing. Everyone had […]
#649: Q&A: Should You Buy a House Now or Invest Your Down Payment Instead?
“Should I buy a home?” Home prices have soared, interest rates remain sticky, and many first-time buyers feel like they’re watching the train pull out of the station. If you’ve saved for years but can’t afford a home nearby, should you stretch to buy (maybe hours away) or invest that cash instead?
In this episode, […]
I Paid Rent Today. I Also Collected Rent.
I paid rent today. I also collected rent today.
Ever since I moved to New York City, I’ve had this uncommon experience on the first of every month. It flies in the face of how society teaches us to adult.
The conventional thinking is that a person graduates from college, gets a […]
#645: Q&A: My Friend Won’t Invest – How Can I Help?
Mike: After 15 years of intentional living, Mike is 80 percent of the way to financial independence. Now he’s trying to help friends take control of their own financial future. But what happens when one spouse is eager to learn and invest, while the other isn’t interested?
Michael: For two years, Michael has tracked his […]
#579: I Have 14 Days Until My Tenants Move In … And Nowhere to Go
Todd is in a real estate bind. He found out six days before closing on a new home that it wasn’t legally sellable. And renters are moving into his current home in two weeks. What should he do?
Anonymous is excited about expanding her real estate portfolio. Should she sell her $2.5 million rental property in the Bay Area to do this, or can she keep it and leverage the equity instead?
Former financial planner Joe Saul-Sehy and I tackle these two questions in today’s episode.
Enjoy!
